


Thigh-Highs, Garters, and Heels

by jaradel



Series: Check Please Twitfics [1]
Category: Check Please! (Webcomic)
Genre: Anal Sex, Fingering, High Heels, Lingerie, M/M
Language: English
Status: Completed
Published: 2016-10-17
Updated: 2016-10-17
Packaged: 2018-08-23 00:54:52
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,560
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8307595
Author URL: https://archiveofourown.org/users/jaradel/pseuds/jaradel
Summary: Jack loves to buy Bitty lingerie. But a pair of red-soled heels are something else.





	

**Author's Note:**

> This is the first in a series of expanded twitfics from my Twitter. My good friend [tiptoe39](http://archiveofourown.org/users/tiptoe39) suggested that I post these to Tumblr, and then I decided that I'd quite like to use them as prompts for drabbles and ficlets. 
> 
> Disclaimer: Characters belong to [Ngozi](http://ngoziu.tumblr.com), creator of [Check Please!](http://omgcheckplease.tumblr.com)
> 
> Many thanks to [tiptoe39](http://archiveofourown.org/users/tiptoe39) and [marswithghosts](http://archiveofourown.org/users/marswithghosts) for looking this over!

* * *

 

 

It started on Jack's birthday, when Bitty surprised him by wearing light blue satin bikini panties. There was something about seeing Bitty's small but very masculine body in delicate feminine lingerie that made him incredibly aroused. And so Jack began to buy things for Bitty to wear for him, lace panties and silk stockings and matching garter belts, and Bitty enthusiastically modeled them for Jack, who enthusiastically peeled them off of Bitty and fucked him soundly into the bed.

This, though, this is something they haven't tried before.

"Jack, these are Louboutins! They cost a small fortune!"

Jack's face heats up. "I - I saw them when I was looking for heels for you, and I liked the red soles. I thought they'd look good on you. Do you not like them?"

"Jack, I _love_ them! I just worry about you spending so much money for a pair of shoes that I'll only ever be able to wear here."

"I think I'm good for it. I want you to have nice things. Even if you and I are the only people who see them."

Jack gets an armful of Bitty just then, as Bitty jumps up to hug him. "You sweet, ridiculous man. Have I told you how much I love you?"

Jack grins. "Not today."

Bitty playfully swats Jack on the shoulder. "Well, I love you more than I can ever say." He kisses Jack soundly, and having Bitty pressed against him like this is getting his motor running. Bitty slides down until he's standing on the floor, and gives Jack a wicked grin. "So, should I try them on? How do you want me?"

 _Every way imaginable_ , Jack thinks. "Ah, can you wear them with the stockings and the garter belt? But nothing else?" He can feel his face flame with embarrassment.

Bitty's cheeks flush with arousal, and his grin gets wider, more saucy. "Of course, honey. You wait right here."

Jack sits down on the bed as Bitty takes the heels inside the walk-in closet. In one of the drawers that Jack had carefully set aside for Bitty's spare clothes, folded neatly, are the silk stockings and lace garter belt that Jack bought for him. Bitty closes the door with a wink, leaving Jack to imagine what's happening on the other side. And oh, does Jack imagine. He imagines Bitty stripping off all of his clothes, sitting down on the dressing bench to pull the stockings on over his long legs, fastening the garter belt around his waist, and attaching the straps to the stockings. He imagines Bitty sliding his feet into those red-soled heels and standing up, admiring himself in the mirror on the back of the closet door, turning this way and that to see how the heels accentuate his calves. He imagines Bitty's cock framed by the lace garter and the straps, hard and curving upward over the front panel of the garter belt. He palms his own cock through his shorts, groaning at the mental image.

The door opens, and Jack's eyes go wide. Reality is so much better than imagination. Bitty stands in the door frame, hip cocked to one side and his hand on his waist, that wicked grin playing across his face. "Well, what do you think?"

Jack stands, and closes the distance between them, and that's when he realizes that the heels have an unintended benefit of bringing Bitty almost level with Jack. He doesn't have to lean down to kiss Bitty, or fully extend his arm to wrap his hand around Bitty's hard cock. He's never had an issue with Bitty's height; on the contrary, he rather likes that Bitty is shorter than him, but this is something new, something exciting. And it gives Jack a number of ideas.

"God, you're gorgeous," he says between kisses, as Bitty presses his nearly naked body to Jack's clothed one. "So much I want to do with you."

Bitty's laugh is low and sultry. "I'm all yours, honey. However you want me."

"Are you sure?" Jack is nothing if not a gentleman, and he doesn't want to make Bitty uncomfortable.

"Of course I'm sure! I trust you, Jack, completely." Bitty punctuates the statement with a long, slow, deep kiss that makes Jack's toes tingle.

"Ahhhh, _mon Dieu, cher_ ," Jack groans. "Can't think straight when you do that."

"That's sort of the point, sweetheart."

Jack starts walking Bitty towards the bed, surprised at how well Bitty is walking in the heels, and that sends another pulse of arousal through his cock. "Want to bend you over," he says. "Want to fuck you."

"Oh Lord, yes, yes Jack," Bitty gasps, and Jack can feel Bitty's cock twitching against him. Jack steps back just long enough to strip off his clothes, and Bitty bends over the edge of the bed, pulling a couple pillows over so he can lean on them with his forearms. "Like this?"

"Yeah, just like that," Jack says, his voice rough. He steps behind Bitty, stroking Bitty's back from his neck to the edge of the lace garter belt. Bitty shivers, and Jack gentles him, stroking his hands along Bitty's sides, over his hips, down his thighs between the straps of the belt. His hands move up and over Bitty's ass, kneading and squeezing the well-developed muscles there. Bitty moans, pushing back into Jack's hands.

"Honey, _please_ ," Bitty whines, shaking his ass for good measure.

Jack doesn't need to be told twice. He opens the nightstand drawer and pulls out the bottle of lube and a condom. He coats three fingers with lube and sets the bottle on the nightstand, rubbing his fingers together to warm them up. Grasping Bitty's hip with his left hand, he uses his right middle finger to gently massage Bitty's hole, which flutters under his fingertip. Slowly, carefully, he pushes in, turning his finger and pulling it almost all of the way out before gently pushing back in again. He wants Bitty well prepared for this.

Bitty moans wantonly at the initial intrusion, tensing up at first, but relaxing as Jack sets a slow, steady rhythm. When Bitty feels relaxed enough, Jack slips his index finger in alongside his middle finger, gently, softly, sliding in and letting Bitty's body get used to the feeling. Bitty's trembling ever so slightly, and Jack pets Bitty's side, leaning over Bitty to press soft kisses along his spine. He carefully scissors his fingers, working Bitty open. Bitty is whimpering, pressing back on Jack's hand, his cock dripping precome onto the duvet, and Jack thinks this is the sexiest thing he's ever seen. He nudges a third finger in, twisting, pushing, pulling, and Bitty is crying out, asking for more, asking for Jack to fuck him, please, _now_.

Jack pulls his fingers out and hastily opens the condom, rolling it on and using more lube to slick it up. He grasps Bitty's hip again and lines himself up, the heels negating the need for him to lean over or bend his knees. "Are you ready?" he asks, voice almost cracking with pent-up want.

"Yes, Jack, yes _please_ ," Bitty cries, thrusting his ass back toward Jack's cock.

Jack guides himself into Bitty's hole, and once the head of his cock is inside, he stops, grasping Bitty's other hip. Bitty is panting. "Give me a sec," he says, breathless, and then Jack feels him relax. "Okay."

Jack holds Bitty's hips as he slides in fully, Bitty's ass snug against his hips, and now it's his turn to stop for a minute, before he comes right then and there. He takes a deep breath, and then another.

"Honey, please, move," Bitty gasps, pushing back on Jack's cock.

Jack slides out and back in slowly, and both of them groan. This surely won't last long, but oh God, does it feel heavenly. Jack sets a steady pace, not wanting to hurt Bitty, but Bitty has other plans, as he keeps meeting Jack's thrusts with his ass. and whimpering more, more. Jack loses the last shreds of his self-control and grips Bitty's hips hard, fucking him with reckless abandon. Bitty reaches down and grabs his cock, jerking off in time with Jack's thrusts, and holy hell, seeing Bitty's back and arm muscles move like that is hotter than Jack could have ever imagined. He can feel his orgasm building, a tingling spreading out from the base of his spine as he chases it, and then--

Bitty comes with a shout, spurting all over the bed and clenching his hole, and that does it for Jack, as he buries his cock in Bitty's ass and comes so hard his vision whites out. One moment every muscle in his body is tense, and the next, his limbs feel like jelly. He grasps the base of his cock and pulls out slowly, entranced by the way Bitty's hole remains open for a second or two before slowly closing. Bitty slides forward until he's laying across the bed; the Louboutins fall off his feet and he groans with pleasure. Jack disposes of the condom and lays down next to Bitty, pulling him against his chest.

"Was that--"

"Yes, yes it was," Bitty replies with a laugh. "It most certainly was."

"So you like the shoes?"

"I LOVE the shoes. And apparently, so do you."

"I really do. Especially on you."

**Author's Note:**

> The shoes in question: http://us.christianlouboutin.com/us_en/shop/women/corneille-100-veau-velours-veau-velours.html


End file.
